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Preparation method of polysubstitution dihydrofuran [2,3-b] pyridine derivative

A dihydrofuran, multi-substitution technology, applied in directions such as organic chemistry, can solve problems such as long processing steps, low yield, harsh reaction conditions, etc., and achieve the effects of short reaction time, high yield, and easy post-processing

Active Publication Date: 2017-06-23
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many limitations in traditional synthetic methods, such as harsh reaction conditions, lengthy processing steps, low yield, and the need for functionalized pyridine compounds as starting materials, etc.

Method used

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  • Preparation method of polysubstitution dihydrofuran [2,3-b] pyridine derivative
  • Preparation method of polysubstitution dihydrofuran [2,3-b] pyridine derivative
  • Preparation method of polysubstitution dihydrofuran [2,3-b] pyridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of 2,4,6-triphenyl-2,3-dihydrofuro[2,3-b]pyridine

[0026]

[0027] Add 1mmol of 1,3-diphenyl-3-propargylamino-2-alkene-1-one, 2mmol of benzaldehyde, and 1mL of dimethyl sulfoxide into a 5mL reaction tube, react at room temperature for 15-30min; add appropriate amount of water Or sodium chloride solution to stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 It was dried, filtered, concentrated, and the target product was purified by column chromatography (silica gel, 5% ethyl acetate / petroleum ether). The compound is characterized as follows: white solid; (99mg, 57%); m.p.143-145°C; -1 ; 1 H NMR (400MHz, CDCl 3 )δ8.06(d, J=7.5Hz, 2H), 7.55(d, J=7.4Hz, 2H), 7.50-7.34(m, 12H), 5.92-5.85(m, 1H), 3.82(dd, J =16.4, 9.4Hz, 1H), 3.37(dd, J=16.4, 7.8Hz, 1H); 13 C NMR (100MHz, CDCl 3 )δ 168.76, 155.93, 147.49, 141.34, ...

Embodiment 2

[0029] Preparation of 2-(2-fluorophenyl)-4,6-diphenyl-2,3-dihydrofuro[2,3-b]pyridine

[0030]

[0031] Add 1mmol of 1,3-diphenyl-3-propargylamino-2-alkene-1-one, 2mmol of 2-fluorobenzaldehyde, and 1mL of dimethyl sulfoxide into a 5mL reaction tube, and react at room temperature for 15-30min; Add appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 It was dried, filtered, concentrated, and the target product was purified by column chromatography (silica gel, 5% ethyl acetate / petroleum ether). The compound is characterized as follows: white solid; yield: (80mg, 43%); m.p.140-142°C; -1 ; 1 H NMR (400MHz, CDCl 3 )δ8.11-8.03 (m, 2H), 7.63 (td, J=7.6, 1.4Hz, 1H), 7.59-7.53 (m, 2H), 7.52-7.36 (m, 7H), 7.33-7.27 (m, 1H), 7.16(td, J=7.6, 1.0Hz, 1H), 7.11-7.04(m, 1H), 6.18-6.06(m, 1H...

Embodiment 3

[0033] Preparation of 2-(2-methylphenyl)-4,6-diphenyl-2,3-dihydrofuro[2,3-b]pyridine

[0034]

[0035] Add 1mmol of 1,3-diphenyl-3-propargylamino-2-alkene-1-one, 2mmol of 2-methylbenzaldehyde, and 1mL of dimethyl sulfoxide into a 5mL reaction tube, and react at room temperature for 15-30min ; Add appropriate amount of water or sodium chloride solution to stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 It was dried, filtered, concentrated, and the target product was purified by column chromatography (silica gel, 5% ethyl acetate / petroleum ether). The compound is characterized as follows: white solid; yield: (118mg, 65%); m.p.183-185°C; -1 ; 1 H NMR (400MHz, CDCl 3 )δ8.08(d, J=7.8Hz, 2H), 7.61-7.55(m, 1H), 7.55-7.50(m, 2H), 7.49-7.37(m, 7H), 7.23-7.15(m, 3H) , 6.04(dd, J=9.4, 7.7Hz, 1H), 3.83(dd, J=16.3, 9.5Hz, 1H), 3.23(dd, J=16...

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Abstract

The invention discloses a preparation method of a polysubstitution dihydrofuran [2,3-b] pyridine derivative. A structural formula of the polysubstitution dihydrofuran [2,3-b] pyridine derivative is shown in the description, wherein R1 is hydrogen, phenyl, substituted phenyl, pyridine, substituted pyridine, furan, substituted furan, thiophene or substituted thiophene; R2 is phenyl, substituted phenyl, pyridine, substituted pyridine, furan, substituted furan, thiophene or substituted thiophene; R3 is phenyl, substituted phenyl, pyridine, substituted pyridine, furan, substituted furan, thiophene or substituted thiophene. The preparation method can be used for synthesizing multiple polysubstitution dihydrofuran [2,3-b] pyridine derivatives which cannot be easily obtained by other synthesizing methods.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of multi-substituted dihydrofuro[2,3-b]pyridine derivatives. Background technique [0002] Dihydrofuro[2,3-b]pyridine derivatives are an important class of nitrogen-containing heterocyclic compounds with a wide range of pharmaceutical activities, and have important applications in anti-cancer, anti-inflammatory, anti-tumor, and anti-senile dementia drugs value. Therefore, the research on new synthesis methods of dihydrofuro[2,3-b]pyridine compounds and their derivatives has important application value and has attracted the attention of researchers in related fields. [0003] The traditional synthesis method of polysubstituted dihydrofuro[2,3-b]pyridine usually uses functionalized pyridine compound as the starting material, and synthesizes polysubstituted dihydrofuro[2,3-b]by intramolecular nucleophilic substitution reaction or D-A react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048
CPCC07D491/048
Inventor 程国林翁云翔
Owner HUAQIAO UNIVERSITY